It has been said that “the shortest distance between two people is a story.” That quote, attributed to author Patti Digh, captures something I’ve come to believe deeply through my work as a leadership search consultant: stories build bridges. And if you're a school leader considering your next move, you already have a story to tell. The key is learning how to tell it well.

In my years supporting school leaders in the search process, I’ve interviewed thousands of educators, and I almost always begin the same way: “Tell me the story behind your resume.” It’s a deceptively simple prompt, but what follows often determines how memorable and compelling a candidate will be—not just in that first impression, but throughout the hiring process. For many, the character Sam-I-Am from Dr. Seuss’s Green Eggs and Ham was likely one of the first we encountered as young readers. Did they leave an indelible impression on you, too?

For some, the story flows naturally. For others, it takes time and revision. That’s why I’ve come to believe that storytelling is not just a helpful career skill, it’s a leadership skill, one that should be cultivated just as intentionally as budgeting, hiring, or curriculum design.

All educators tell stories in classrooms as we engage students in the material and curriculum. Honing this skill intentionally is key to transitioning into an administrative role—particularly as a divisional leader or Head of School—as we work to engage all our constituents in the story behind the critical work being done across the school and within the community.

Leadership searches, particularly in independent schools, are about alignment. Search committees want to know not just what you’ve done, but who you are, and how your experience, values, and perspective intersect with the school’s own journey. This is where storytelling becomes critical.

A well-told story can:

· Illuminate how your personal and professional paths have converged over time

· Highlight moments of growth and decision-making

· Demonstrate the motivations behind your career transitions

· Show how you see yourself in the context of a school’s mission

Put simply: a résumé lists your milestones, but a story explains your “why.”

My own “story” includes several years pursuing a Master of Fine Arts in creative writing, as well as time spent teaching composition and creative writing at a community college. In writing courses, we often teach students to pay attention to the basic components of narrative: character, plot, tone, and audience.

These same elements are useful when crafting your leadership narrative:

· Character: Who are you? What drives your decisions? What kind of leader are you becoming?

· Plot: What events—successes, pivots, even failures—have shaped your path?

· Tone: What’s the emotional undercurrent of your story? Are you sharing with humility, confidence, and curiosity?

· Audience: Who are you talking to? A search committee? A head of school? A board?

Your “professional short story” doesn’t need to be long. In fact, the most effective ones are tightly focused, authentic, and tailored to the moment. That may mean different versions for different opportunities, each rooted in the same truth but shaped for a particular audience.

And just as in writing, revision is everything. With practice, your story becomes clearer, more resonant, and more aligned with the schools you’re targeting.

Consider a simple exercise: practice telling your story to a trusted peer or colleague. Strive to receive structured feedback by asking them to listen and then share three aspects of the story that stood out, two places that were unclear, and one part that could be trimmed. Modeled after the kind of feedback you'd receive in a writing workshop, the process can be ongoing, and the goal is continued refinement.

The best storytellers I’ve encountered as candidates are not just articulate—they are strategic. They understand how to align their personal and professional narratives with the values, vision, and trajectory of the schools they are applying to.

When a candidate can say, “Here’s how I’ve grown, here’s what I’ve learned, and here’s why your school is the next chapter of that story,” it creates a moment of clarity for the committee. It helps them see you not just as a résumé, but as a potential partner in their work.

Even beyond the job search, storytelling remains a powerful leadership tool. Whether you're inspiring faculty, engaging with parents, or making a case for strategic change, your ability to connect through story builds trust and strengthens relationships.

So, what's your story? And just as importantly, how are you telling it?